What are the biggest Social Security and retirement mistakes retirees make? Toby Mathis and Erin Moriarity break down when to claim Social Security, Social Security taxes, Roth conversions, Medicare and IRMAA surcharges, the 4% rule, retirement income strategies, long-term care costs, and how to avoid running out of money in retirement. 

Learn how smarter Social Security planning, Medicare planning, tax strategies, and retirement withdrawal decisions can help you build a more secure retirement. 

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Medicare Resource Mentioned in This Video: https://askchapter.org/ 

Many people do not realize how much of their social security benefits may be taxable until it is too late. 

By identifying these frequent social security taxes issues early, you can adjust your strategy to keep more of your money. This discussion is designed for anyone approaching retirement age who wants to avoid costly errors.

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Chapters:

Trader Status has far more tax-saving potential than most investors realize, going well beyond basic investment deductions in this insightful conversation with tax experts Toby Mathis and Jeff Cottle from Anderson Advisors.

Interested in learning more about tax strategies for traders? Schedule a free consultation here 👉 https://aba.link/mwi8

Learn the key differences between an investor and a trader under IRS rules and why qualifying for Trader Tax Status can allow you to deduct expenses like software, education, and trading equipment. 

They'll breaks down how active traders can potentially save thousands in taxes by being treated as a business instead of a passive investor. 

If you trade stocks, options, or crypto, this is essential tax planning information you need to know.

Show Notes:

In this episode, Anderson attorneys Amanda Wynalda, Esq., and Eliot Thomas, Esq., answer listener questions on tax planning, entity structuring, and asset protection for real estate investors. They discuss the best tax strategies for investors who own multiple rental properties as sole proprietors and examine whether converting an S Corporation that owns rental property into an LLC could trigger property tax reassessments or other tax consequences. Amanda and Eliot also explain the rules surrounding home office deductions, including using a detached ADU as a dedicated workspace and claiming deductions for business storage in a garage. They cover the differences between operating as an S Corporation with an accountable plan versus filing on Schedule C, addressing common concerns about IRS scrutiny. Finally, they explore the complexities of structuring a 1031 exchange alongside a self-directed Solo 401(k), highlighting prohibited transaction rules, financing considerations, and strategies for staying compliant while maximizing tax benefits. Tune in for practical guidance on protecting your investments and making informed tax decisions.

Submit your tax question to [email protected]

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Highlights/Topics:

0:00 Intro

9:29 I work in a family-owned company and have the opportunity at the end of this year to obtain equity/ownership. Would you recommend accepting that ownership under a specific tax strategy or corporate setup, or just accepting the ownership under my name and Social Security number?

18:26 Is it a good idea to pull money from a traditional IRA early and then invest in oil funds to get IDC deductions to help offset the taxes I will incur by withdrawing from the IRA?

23:25 Can tax documents be reviewed for previous years and if my previous preparer didn’t use all the available strategies; can those strategies be applied for those years?

27:32 I will be relocating to South Africa which has a tax treaty with the United States Government. I am a retiree who receives a monthly annuity. Will I be double taxed? I will be paying both federal and state taxes in the USA.

34:36 What is the best tax strategy for sole proprietor ownership of 12 rentals?

40:50 I have a 22-unit condo project that we converted into rentals in 1992. It was a C Corp. Now it is an S corp. One adviser suggested converting to an LLC. Would this trigger a taxable event for property tax assessments?

47:23 I have a detached ADU in my backyard. I want to use it as a home office. Can I do that and if so, how is the deduction calculated? Also, can I get a deduction if I use part of my garage for the business for storage?

53:59 Does a Sub-S election with an accountable plan attract more attention than a Schedule C filer?

57:07 We are completing a 1031 exchange and would like guidance on the best way to structure the purchase of our replacement property. Our objective is to use all available 1031 exchange proceeds while funding the remaining balance with assets from a self-directed Solo 401(k), if permissible, and avoid obtaining a conventional mortgage. Are there any IRS rules, prohibited transaction concerns, or tax implications we should be aware of before proceeding?

Want to build a million-dollar retirement without guessing on stocks? In this video, Toby Mathis, Esq. is joined by Eliot Thomas, Esq. of Anderson Business Advisors to break down how the type of account you use—like a taxable brokerage account versus an IRA or 401(k)—can make a massive difference in how fast your money grows. 

Would you like to learn more about protecting your assets and minimizing taxes? Schedule a free consultation here 👉 https://aba.link/zpgs

Register for a FREE upcoming workshop today if you want to protect your personal assets from creditors. Save Your Seat 👉 https://aba.link/puv3 

You’ll learn how taxes impact your investments, and why strategies like tax deferral and Roth accounts can help you keep more of what you earn. 

They also cover how certain plans let you contribute far more than most people realize, sometimes even hundreds of thousands per year. 

If you’re serious about growing your wealth and understanding how retirement accounts actually work, this is a must-watch.

Show Notes:

00:00 Introduction

In this Tax Tuesday episode, Anderson Advisors' Barley Bowler, CPA, and Eliot Thomas, Esq., answer listener questions covering entity structuring, real estate tax planning, investing, and charitable giving strategies. They explain when it makes sense to form an LLC or S Corporation for a real estate flipping business and whether new investors should wait until after closing their first deal. They also discuss how profits earned inside an LLC trading stocks and stock options are taxed, and whether leaving funds in a brokerage account changes the tax treatment.

Barley and Eliot break down whether a cost segregation study makes sense for a long-held commercial property undergoing significant capital improvements, and how that decision compares to selling the property, completing a 1031 exchange, and performing a cost segregation study on replacement assets. They also explore tax-efficient charitable giving strategies, including ways to contribute appreciated assets or funds designated for charity while minimizing capital gains taxes. Tune in for practical guidance on these tax-saving strategies and more!

Submit your tax question to [email protected]

Resources

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Chapters:

0:00 Intro

9:32 Please speak about vacation rentals that are considered primary residences. We will rent our new property out in the summer months while we are at our secondary residence and stay there in the winter months (so we can’t take advantage of the STR loophole). What tax strategies are available to us in the above case?

17:03 We are selling our company at the end of July 2026. Usually this would be treated as long-term capital gain (taxed at 23.8%) but because I haven't been with the company for 12 months, I believe I would be taxed as ordinary income. Could I invest those funds in a Qualified Opportunity Zone to avoid paying ordinary taxes? Are there new rules with OBBBA that will take effect January 1, 2027?

27:03 I have a C Corporation that earns income from management fees normally paid annually from the LLCs the C Corp manages. During the last C Corp fiscal year, no management fees were paid due to the LLC not having income. Does the C Corp still need to file a tax return if it has no income, and does this mean the C Corp cannot pay any reimbursements for this tax year?

31:45 Please explain the details of when you sell a stock at a loss and repurchase the same stock within 30 days. (Wash Sale Rules)

35:57 At what point do I need to form an LLC or S-Corp for my real estate flipping business? I am just starting in the market and was told not to worry about it until I made my first deal. Is that true?

39:45 I have an LLC for trading stock options and stocks. If I make $1,000,000 profit and do not transfer it out of my brokerage account to me personally, is this money taxed, or is it taxed when I do pull it out of the account?

45:15 I am the managing partner of a general partnership that owns a strip center for many years with little depreciation left. We are spending about $500,000 on a new roof and paving to put a big-box tenant in a long-standing vacancy. Would a cost segregation study benefit here? Should we sell (at a massive profit) and 1031 into new assets and then do the CSS?

51:09 Is there a way to put funds into an account for charity and it not be taxed on gains?

57:23 Can you please explain the non-AFS 417(c) method? Can it be used for an LLC partnership? And can it be used to create a loss, or does the loss carry over to the following tax year?

Interested in learning how to hide your real estate with a land trust? Schedule a free consultation here: https://aba.link/rcvw

In this podcast, Toby Mathis sits down with attorney and asset protection expert Amanda Wynalda to explain why keeping your real estate ownership public can put your finances, privacy, and future at risk.

You’ll learn how lawsuits really happen, why newer investors are often the most vulnerable, and how a single bad tenant situation can spiral into hundreds of thousands of dollars in legal costs.

Toby and Amanda break down how to use land trusts, LLCs, insurance, and privacy strategies work together to help protect real estate investors from unnecessary exposure.

They also explain who actually needs these strategies, common mistakes investors make, and how to create multiple layers of protection around your assets before problems happen.

FREE TAX & ASSET PROTECTION WORKSHOP Register for an upcoming workshop today if you want to protect your business and personal assets from snoopy lawyers and creditors. Save Your Seat: https://aba.link/jyn9

0:00 Intro

Would you like to learn more about protecting your assets and minimizing taxes? Schedule a free consultation here: https://aba.link/964265

Today, we're discussing a significant tax credit, the Eligible Automatic Contribution Arrangement (EACA), which means actual dollars in your pocket, not just a tax deduction.

Savannah Wallace, one of our expert attorneys, joins to explain how this finance strategy can help you save money on taxes. This is crucial personal finance information for anyone looking to optimize their tax planning.

Don’t miss this opportunity to reduce your tax bill and build wealth smarter.

Sign up for a Free Tax & Asset Protection Workshop here: https://aba.link/lx3q

Join Eliot Thomas, Esq. and Amanda Wynalda, Esq. for this Tax Tuesday replay as they discuss whether you can use a 1031 exchange to buy land for a subdivision, key IRS rules to know, and common mistakes investors should avoid.

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Show Notes:

0:00 Intro

8:57 If I sell a rental property, how can I do so, without having to pay capital gains and recapture all the depreciation, or at least minimize the effect of that cash impact? After those tax expenses we will not have much cash left from the sale, if any. Since we only have 1 rental there isn't anything to roll the money into or offset the gains.

18:59 Can I use money from a 1031 exchange to buy land from a lot from another property I subdivide?

21:22 Should I report my capital gains under my name or set up an LLC?

26:10 We are considering purchasing an Airbnb and/or a college rental. We just established an LLC and Trust with Anderson. What are the tax considerations/implications for this?

34:17 When is real estate professional status not beneficial?

40:42 I have an S corporation and am trying to determine what a reasonable wage for myself would be. How do I determine a reasonable wage?

48:11 What is the best tax strategy for your S corporation business renting from yourself? Is it better to lower the rent to yourself and have less rent deduction from 1120S? Are there tax deductions other than property tax and maintenance? Should I form an LLC as a landlord to my business? Or will it make more work filing?

56:24 Are there any ways to shelter interest earned from hard-money lending if the money was lent from personal savings, not under any business entity?

59:15 What can I file to maximize my tax benefits as a 1099 independent contractor?

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Enjoy this full replay of Tax Tuesday.

Show Notes:

10:13 What is the difference between a Public Charity and a Private Foundation?

21:47 I have a single-family residence that I have owned and rented out for 10 years. I want to somehow use it for my public charity. Should I sell it and donate the proceeds or donate the house directly to the nonprofit?

29:37 I have a US-based Public Charity. Can I use it to make donations overseas?

34:01 Can I run an Airbnb out of my Public Charity?

37:49 Am I able to use Artificial Intelligence to fill out IRS Form 1023 to request Federal tax-exempt status?

43:19 I have a rental property in an Opportunity Zone – how can I avoid capital gains tax? That same property has furniture – how do I deduct that?

53:12 I purchased a triplex in December 2025 and self-manage it.  I am actively involved in real estate investing and qualify for Real Estate Professional status.  What are my options as far as cost segregation strategy vs traditional depreciation?

1:03:10 I currently have a rental property which has been depreciated since purchase. I would like to know if it is possible to establish it as my primary residence and the tax impact.  Will I have to repay all the depreciation allowances?

1:07:47 Regarding a guaranteed partner payment to a C Corp management entity from the trading LLC. What is a guideline for the maximum % allowed where the C corporation owns 20% of the LLC?

1:13:06 I make targeted investments in private companies and venture funds via this entity.  What is the role of an 83B designation? What are the rules and timeframe?

In this episode, Anderson Advisors' Barley Bowler, CPA, and Eliot Thomas, Esq., tackle listener tax questions spanning real estate, trading, and business structures. They explain how California's clawback rules and residency tests apply to precious metals gains when relocating to Tennessee, and outline how a trade structure with a corporate partner can shift trading income while avoiding personal holding company tax. Barley and Eliot also cover entity options for leasing a personal vehicle to a business, the filing requirements for out-of-state rental income, and how a property management S-Corp can be used to offset W-2 income through short-term rental material participation. Other topics include strategies for minimizing capital gains on a long-term rental sale — including 1031 exchanges and cost segregation studies — offsetting capital gains from a personal residence sale with business losses, and how non-dividend distributions are taxed as a return of capital. Tune in for expert advice on these and more!

Submit your tax question to [email protected]

00:00 Intro to Tax Tuesday with Eliot and Barley

08:06 — "I've lived in California for decades but am now moving to Tennessee. Once in Tennessee, I will sell some of my precious metals to go toward buying a personal residence. Will California try to claw back taxes on the precious metal gain since I purchased it while living in California? How long do I have to be a resident of Tennessee before I am under Tennessee taxation rules for selling precious metals?" — Clawbacks don't apply; timing and residency ties to California matter most.

18:24 — "As an equity options trader (not eligible for TTS status), what is a good entity structure for tax advantages when my partner has an SMLLC for business?" — A trade structure with a C-Corp partner shifts and protects gains.

26:05 — "I have a trading structure. Please explain the tax treatment guidelines when investments in securities are sold, when a K-1 is triggered, etc." — Gains split by ownership percentage; K-1s issue once the 1065 is filed.

36:05 — "I'm wondering if I can purchase a vehicle and lease it to my business year by year — is that a possible tax advantage for a private investigation business?" — Possible, but reimbursing mileage through an S-Corp is simpler and safer.

44:20 — "I live in Washington State. If I buy a rental in Oregon, do I have to file Oregon tax and pay Oregon tax on the property located there?" — Yes — the source state taxes rental income regardless of residency.

47:02 — "I run three Airbnb properties and have an LLC taxed as an S-Corp that I use as a management company, where all revenue and expenses flow into it. It does not take depreciation since the LLC doesn't own the property — we have the deeds in our personal name. How can I take advantage of the loss and depreciation to offset our W-2 in this case?" — Short-term rentals need material participation, not REP status, to offset W-2.

1:04:27 — "How can I avoid or minimize capital gain taxes if I sell a rental property I've had for seven years?" — Use passive losses, a cost-seg study, 1031 exchange, or capital loss harvesting.

1:10:32 — "Can a long-term capital loss (from the sale of a business) be used to offset a long-term capital gain from the sale of a personal residence?" — Yes, after applying Section 121's home-sale exclusion and depreciation recapture rules.

1:15:24 — "Are non-dividend distributions considered a return of capital and therefore not taxed?" — Only partly — earnings, then basis return, then capital gain, in order.

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